WO2016054959A1 - Crystal form of bisulfate of jak inhibitor and preparation method therefor - Google Patents
Crystal form of bisulfate of jak inhibitor and preparation method therefor Download PDFInfo
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- WO2016054959A1 WO2016054959A1 PCT/CN2015/089223 CN2015089223W WO2016054959A1 WO 2016054959 A1 WO2016054959 A1 WO 2016054959A1 CN 2015089223 W CN2015089223 W CN 2015089223W WO 2016054959 A1 WO2016054959 A1 WO 2016054959A1
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- crystal
- hexahydrocyclopenta
- pyrrolo
- pyrrole
- amino
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Definitions
- the present invention relates to (3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-pyrrolo[2,3- Form I crystal of d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate, and a preparation method and use thereof.
- the compounds of formula (I) obtained according to the process of the invention are useful in the treatment of arthritis.
- Tofacitinib (CP-690550) is a new oral JAK pathway inhibitor developed by Pfizer Inc. Tofacitinib is the first-in-class drug developed for the treatment of rheumatoid arthritis. Since the birth of tofacitinib in Pfizer's own laboratory, the drug has been placed on the high hopes of heavy drugs, the success of the drug will also be a major victory for Pfizer's highly criticized R & D business, after the results of the clinical phase III trial, Pfizer tofacitinib is significantly more effective than methotrexate.
- the crystal structure of the pharmaceutically active ingredient often affects the chemical stability of the drug, and the difference in crystallization conditions and storage conditions may lead to changes in the crystal structure of the compound, sometimes accompanied by the formation of other forms of crystal form.
- amorphous drug products have no regular crystal structure and often have other defects, such as poor product stability, fine crystallization, difficult filtration, easy agglomeration, and poor fluidity. Therefore, it is necessary to improve the various aspects of the above products. We need to study in depth to find new crystal forms with high purity and good chemical stability.
- the form of the compound of the formula (I) which can be used as a raw material is not particularly limited, and any crystal form or amorphous solid can be used, and the type I crystal of the compound of the formula (I) of the present invention
- the preparation method is:
- alcohols having a carbon number of 3 or less are preferred.
- more preferably methanol is used as a recrystallization solvent for the compound of the formula (I).
- the method for preparing Form I crystals of the compound of formula (I) provided by the present invention comprises the steps of:
- the organic solvent is selected from the group consisting of alcohols having a carbon number of 3 or less, and further preferably the organic solvent is methanol.
- the method of recrystallization differs from the usual recrystallization operation method. After the compound of the formula (I) in any form is heated and dissolved in an organic solvent, a part of the solvent is removed by atmospheric distillation, and after completion of the crystallization, it is dried by filtration to obtain a desired crystal.
- the crystals to be collected are usually dried under vacuum at a temperature of about 30 to 100 ° C, preferably 40 to 60 ° C, to obtain an effect of removing the recrystallization solvent.
- the crystal form of the type I crystal of the obtained compound of the formula (I) was examined by differential scanning calorimetry (DSC) and X-ray diffraction pattern measurement, and the solvent residue of the obtained crystal was examined.
- the type I crystal of the compound of the formula (I) prepared according to the process of the present invention does not contain or contains only a relatively low amount of residual solvent, and meets the requirements of the national pharmacopoeia for the residual solvent of the pharmaceutical product, so that the crystal of the present invention can be better.
- the ground is used as a pharmaceutically active ingredient.
- the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising a crystalline form I of the compound of formula (I), said composition further comprising at least one pharmaceutically acceptable carrier, said pharmaceutically acceptable carrier It may be selected from at least one of lactose, mannitol, microcrystalline cellulose, croscarmellose sodium, sodium carboxymethyl starch, hydroxypropylmethylcellulose, povidone, and magnesium stearate.
- the content of the type I crystal in the pharmaceutical composition provided by the present invention is from 0.5 mg to 200 mg.
- Another aspect of the invention relates to the use of a compound of the formula (I) of the invention, Form I, or a pharmaceutical composition of the invention, for the manufacture of a medicament for the treatment of a disease associated with JAK kinase.
- the disease is preferably rheumatoid and rheumatoid arthritis.
- Figure 1 shows an X-ray powder diffraction pattern of a type I crystal of a compound of formula (I) (represented by the code SHR0302 in the figure).
- Figure 2 shows a DSC pattern of the Form I crystal of the compound of formula (I).
- Figure 3 shows an X-ray powder diffraction pattern of an amorphous solid of the compound of formula (I).
- Figure 4 shows a DSC pattern of an amorphous solid of the compound of formula (I).
- Example 1 A sample of the compound of formula (I) was prepared according to the method of Example 2 of the patent (PCT Application No. PCT/CN2014/076794).
- Example 2 the crystal form of the sample of the measurement example 1 was measured.
- the X-ray diffraction spectrum of the solid sample prepared in Example 1 is shown in Fig. 3, and the characteristic peak of the amorphous form is shown.
- the DSC spectrum is shown in Fig. 4, and no melting characteristic absorption peak is observed below 300 ° C, and the product is determined as follows. Amorphous solid.
- the crystals are at about 6.38 (13.85), 10.38 (8.51), 10.75 (8.23), 14.49 (6.11), 15.07 (5.88), 15.58 (5.69), 16.23 (5.46), 17.84 (4.97), 18.81 (4.72), 19.97. (4.44), 20.77 (4.27), 22.12 (4.02), 23.19 (3.83), 24.12 (3.69), 25.51 (3.49), 26.62 (3.35), 27.38 (3.26), 28.56 (3.12), 29.91 (2.99) Characteristic peaks.
- the DSC spectrum is shown in Fig. 2, which has a sharp melting endothermic peak of 220.23 ° C, and this crystal form is defined as the I crystal form.
- Example 1 The amorphous sample prepared in Example 1 and the Form I crystalline product obtained in Example 3 were separately placed in an open position, and examined under illumination (4,500 Lux), heated (40 ° C, 60 ° C), and high humidity (RH 75%, Stability of the sample under RH90%) conditions.
- the sampling time was 5 days and 10 days, and the purity of HPLC was shown in Table 1.
- the stability study showed that the compound of formula (I) type I crystal and amorphous sample were open. Under the condition of mouth placement, the stability under light, high temperature and high humidity conditions showed that high humidity had little effect on the two, but under the conditions of light and high temperature, the stability of type I crystal was significantly better than none. Stereotype the sample.
Abstract
Description
Claims (8)
- 一种(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶,其特征在于使用Cu-Ka辐射,得到以2θ角度和晶面间距表示的X-射线粉末衍射图谱,所述结晶具有如图1所示的X-射线粉末衍射图谱,其中在约6.38(13.85),10.38(8.51),10.75(8.23),14.49(6.11),15.07(5.88),15.58(5.69),16.23(5.46),17.84(4.97),18.81(4.72),19.97(4.44),20.77(4.27),22.12(4.02),23.19(3.83),24.12(3.69),25.51(3.49),26.62(3.35),27.38(3.26),28.56(3.12),29.91(2.99)有特征峰。(3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-pyrrolo[2,3-d Pyrimidine-4-yl)amino) hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate Form I crystal characterized by Cu-Ka radiation, resulting in a 2θ angle and crystal plane An X-ray powder diffraction pattern represented by a pitch having an X-ray powder diffraction pattern as shown in Figure 1, wherein at about 6.38 (13.85), 10.38 (8.51), 10.75 (8.23), 14.49 (6.11), 15.07 (5.88), 15.58 (5.69), 16.23 (5.46), 17.84 (4.97), 18.81 (4.72), 19.97 (4.44), 20.77 (4.27), 22.12 (4.02), 23.19 (3.83), 24.12 (3.69), 25.51 (3.49), 26.62 (3.35), 27.38 (3.26), 28.56 (3.12), 29.91 (2.99) have characteristic peaks.
- 一种制备如权利要求1所述的(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶的方法,所述方法包括下述步骤:A (3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-) as claimed in claim 1. A method of crystallizing Form I of pyrrolo[2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate, the process comprising the following step:1)将任意晶型或无定型的(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐固体加热溶解于适量的有机溶剂中,常压蒸除部分溶剂,析出固体,所述有机溶剂选自碳原子数小于等于3的醇类;1) Any crystal form or amorphous (3aR, 5s, 6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-) Pyrrolo[2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate solid dissolved in an appropriate amount of organic solvent, steamed at atmospheric pressure Excluding a part of a solvent, a solid is precipitated, and the organic solvent is selected from the group consisting of alcohols having a carbon number of 3 or less;2)过滤,洗涤,干燥。2) Filter, wash and dry.
- 根据权利要求2所述的制备方法,其特征在于在步骤1)中所述的有机溶剂为甲醇。The process according to claim 2, wherein the organic solvent in the step 1) is methanol.
- 一种药物组合物,其含有如权利要求1所述的(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶以及药学上可接受的载体。A pharmaceutical composition comprising (3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5- according to claim 1. Form I crystal of methyl (7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate and pharmaceutically acceptable Accepted carrier.
- 根据权利要求4所述的药物组合物,其特征在于其 (3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶的含量为0.5mg~200mg。The pharmaceutical composition according to claim 4, characterized in that (3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-pyrrolo[2,3-d]pyrimidine The content of the type I crystal of -4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate is from 0.5 mg to 200 mg.
- 根据权利要求4所述的药物组合物,其特征在于,所述药学上可接受的载体选自乳糖、甘露醇、微晶纤维素、交联羧甲基纤维素钠、羧甲基淀粉钠、羟丙基甲基纤维素、聚维酮和硬脂酸镁中的至少一种。The pharmaceutical composition according to claim 4, wherein the pharmaceutically acceptable carrier is selected from the group consisting of lactose, mannitol, microcrystalline cellulose, croscarmellose sodium, sodium carboxymethyl starch, At least one of hydroxypropylmethylcellulose, povidone, and magnesium stearate.
- 根据权利要求1所述的(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶或根据权利要求4所述的药物组合物在制备治疗与JAK激酶有关的疾病的药物中的用途。(3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-pyrrolo[] according to claim 1 Form I crystal of 2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate or the pharmaceutical composition according to claim 4 Use in the preparation of a medicament for the treatment of a disease associated with JAK kinase.
- 根据权利要求1所述的(3aR,5s,6aS)-N-(3-甲氧基-1,2,4-噻二唑-5-基)-5-(甲基(7H-吡咯并[2,3-d]嘧啶-4-基)氨基)六氢环戊并[c]吡咯-2(1H)-甲酰胺硫酸氢盐的I型结晶或根据权利要求4所述的药物组合物在制备治疗风湿及类风湿性关节炎的药物中的用途。 (3aR,5s,6aS)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7H-pyrrolo[] according to claim 1 Form I crystal of 2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide hydrogensulfate or the pharmaceutical composition according to claim 4 Use in the preparation of a medicament for the treatment of rheumatoid arthritis and rheumatoid arthritis.
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
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CA2963581A CA2963581C (en) | 2014-10-09 | 2015-09-09 | Crystal form of bisulfate of jak inhibitor and preparation method therefor |
JP2017517304A JP6830888B2 (en) | 2014-10-09 | 2015-09-09 | Crystal form of hydrogen sulfate of JAK inhibitor and its production method |
RU2017114689A RU2704795C2 (en) | 2014-10-09 | 2015-09-09 | Crystalline form of inhibitor bisulphate jak and method for production thereof |
BR112017005564A BR112017005564A2 (en) | 2014-10-09 | 2015-09-09 | jak inhibitor bisulfate crystal form and method of preparation thereof |
US15/516,529 US10150770B2 (en) | 2014-10-09 | 2015-09-09 | Crystal form of bisulfate of JAK inhibitor and preparation method therefor |
DK15849469.0T DK3205653T3 (en) | 2014-10-09 | 2015-09-09 | CRYSTAL FORM OF BACK SULPHATE OF JAK INHIBITORS AND METHOD OF MANUFACTURE THEREOF |
KR1020177011477A KR20170057441A (en) | 2014-10-09 | 2015-09-09 | Crystal Form of Bisulfate of JAK Inhibitor and Preparation Method Therefor |
AU2015330554A AU2015330554B2 (en) | 2014-10-09 | 2015-09-09 | Crystal form of bisulfate of JAK inhibitor and preparation method therefor |
EP15849469.0A EP3205653B1 (en) | 2014-10-09 | 2015-09-09 | Crystal form of bisulfate of jak inhibitor and preparation method therefor |
CN201580008157.1A CN105980389B (en) | 2014-10-09 | 2015-09-09 | A kind of crystal form of disulfate of jak kinase inhibitor and preparation method thereof |
ES15849469T ES2836100T3 (en) | 2014-10-09 | 2015-09-09 | JAK inhibitor bisulfate crystalline form and method of preparation of the same |
Applications Claiming Priority (2)
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CN201410529863.8A CN105566327A (en) | 2014-10-09 | 2014-10-09 | JAK kinase inhibitor bisulfate crystal type I and preparation method thereof |
CN201410529863.8 | 2014-10-09 |
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WO2016054959A1 true WO2016054959A1 (en) | 2016-04-14 |
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PCT/CN2015/089223 WO2016054959A1 (en) | 2014-10-09 | 2015-09-09 | Crystal form of bisulfate of jak inhibitor and preparation method therefor |
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US (1) | US10150770B2 (en) |
EP (1) | EP3205653B1 (en) |
JP (1) | JP6830888B2 (en) |
KR (1) | KR20170057441A (en) |
CN (2) | CN105566327A (en) |
AU (1) | AU2015330554B2 (en) |
BR (1) | BR112017005564A2 (en) |
CA (1) | CA2963581C (en) |
DK (1) | DK3205653T3 (en) |
ES (1) | ES2836100T3 (en) |
HU (1) | HUE052924T2 (en) |
PT (1) | PT3205653T (en) |
RU (1) | RU2704795C2 (en) |
TW (1) | TWI675839B (en) |
WO (1) | WO2016054959A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018133823A1 (en) * | 2017-01-20 | 2018-07-26 | 江苏恒瑞医药股份有限公司 | Crystal form of bisulfate of jak kinase inhibitor, and preparation method therefor |
CN109563097A (en) * | 2016-11-23 | 2019-04-02 | 无锡福祈制药有限公司 | A kind of crystal form of 7H- pyrrolo- [2,3-d] pyrimidines, salt form and preparation method thereof |
CN111205290A (en) * | 2018-11-22 | 2020-05-29 | 江苏恒瑞医药股份有限公司 | Crystal form of JAK kinase inhibitor and preparation method thereof |
US10786507B2 (en) | 2016-02-19 | 2020-09-29 | Jiangsu Hengrui Medicine Co., Ltd. | Pharmaceutical composition containing JAK kinase inhibitor or pharmaceutically acceptable salt thereof |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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DK3216790T3 (en) | 2014-11-05 | 2019-11-25 | Jiangsu Hengrui Medicine Co | CRYSTALLIC FORM OF JAK CHINESE INHIBITOR-BISULPHATE AND A PROCEDURE FOR PREPARING THEREOF |
MX2023001259A (en) | 2020-07-28 | 2023-05-15 | Arcutis Biotherapeutics Inc | Topical formulation containing jak inhibitor and laureth-4. |
WO2022108913A1 (en) | 2020-11-17 | 2022-05-27 | Arcutis Biotherapeutics, Inc. | Compositions and methods for deep dermal drug delivery |
TW202320788A (en) * | 2021-08-12 | 2023-06-01 | 大陸商江蘇恒瑞醫藥股份有限公司 | Pyrrole six-membered heteroaromatics for the treatment or prevention of anti-host disease |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1439010A (en) * | 2000-06-26 | 2003-08-27 | 辉瑞产品公司 | Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents |
CN1798559A (en) * | 2003-04-04 | 2006-07-05 | 诺瓦提斯公司 | Quinoline-2-one-derivatives for the treatment of airways diseases |
WO2013091539A1 (en) * | 2011-12-21 | 2013-06-27 | 江苏恒瑞医药股份有限公司 | Pyrrole six-membered heteroaryl ring derivative, preparation method therefor, and medicinal uses thereof |
WO2014194741A1 (en) * | 2013-06-07 | 2014-12-11 | 江苏恒瑞医药股份有限公司 | Bisulfate of janus kinase (jak) inhibitor and preparation method therefor |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004057195A1 (en) * | 2004-11-26 | 2006-06-01 | Wilex Ag | Crystalline modifications of N-alpha (2,4,6-triisopropylphenylsulfonyl) -3-hydroxyamidino- (L) -phenylalanine-4-ethoxycarbonylpiperazide and / or salts thereof |
WO2006073292A1 (en) * | 2005-01-06 | 2006-07-13 | Cj Corporation | Inorganic acid salts of sibutramine |
TWI405756B (en) * | 2005-12-21 | 2013-08-21 | Array Biopharma Inc | Novel hydrogen sulfate salt |
EP2691395B1 (en) * | 2011-03-28 | 2017-08-30 | ratiopharm GmbH | Processes for preparing tofacitinib salts |
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2014
- 2014-10-09 CN CN201410529863.8A patent/CN105566327A/en active Pending
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2015
- 2015-09-09 BR BR112017005564A patent/BR112017005564A2/en not_active Application Discontinuation
- 2015-09-09 US US15/516,529 patent/US10150770B2/en active Active
- 2015-09-09 WO PCT/CN2015/089223 patent/WO2016054959A1/en active Application Filing
- 2015-09-09 KR KR1020177011477A patent/KR20170057441A/en active IP Right Grant
- 2015-09-09 RU RU2017114689A patent/RU2704795C2/en active
- 2015-09-09 EP EP15849469.0A patent/EP3205653B1/en active Active
- 2015-09-09 JP JP2017517304A patent/JP6830888B2/en active Active
- 2015-09-09 AU AU2015330554A patent/AU2015330554B2/en not_active Ceased
- 2015-09-09 CN CN201580008157.1A patent/CN105980389B/en active Active
- 2015-09-09 PT PT158494690T patent/PT3205653T/en unknown
- 2015-09-09 CA CA2963581A patent/CA2963581C/en active Active
- 2015-09-09 ES ES15849469T patent/ES2836100T3/en active Active
- 2015-09-09 DK DK15849469.0T patent/DK3205653T3/en active
- 2015-09-09 HU HUE15849469A patent/HUE052924T2/en unknown
- 2015-09-17 TW TW104130773A patent/TWI675839B/en active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1439010A (en) * | 2000-06-26 | 2003-08-27 | 辉瑞产品公司 | Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents |
CN1798559A (en) * | 2003-04-04 | 2006-07-05 | 诺瓦提斯公司 | Quinoline-2-one-derivatives for the treatment of airways diseases |
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RU2017114689A3 (en) | 2019-01-22 |
BR112017005564A2 (en) | 2017-12-12 |
CN105566327A (en) | 2016-05-11 |
EP3205653A4 (en) | 2018-06-20 |
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US20180237438A1 (en) | 2018-08-23 |
CN105980389B (en) | 2017-12-19 |
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US10150770B2 (en) | 2018-12-11 |
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JP2017530146A (en) | 2017-10-12 |
CA2963581C (en) | 2022-07-12 |
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HUE052924T2 (en) | 2021-06-28 |
AU2015330554A1 (en) | 2017-04-27 |
AU2015330554B2 (en) | 2020-01-02 |
DK3205653T3 (en) | 2021-01-11 |
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